Molecules

22 pages, 1461 KiB

Open AccessArticle

GC Analysis, Anticancer, and Antibacterial Activities of Secondary Bioactive Compounds from Endosymbiotic Bacteria of Pomegranate Aphid and Its Predator and Protector

by Taghreed Alsufyani, Najwa Al-Otaibi, Noura J. Alotaibi, Nour Houda M’sakni and Eman M. Alghamdi

Molecules 2023, 28(10), 4255; https://doi.org/10.3390/molecules28104255 - 22 May 2023

Cited by 2 | Viewed by 2271

Abstract

Bacterial secondary metabolites are a valuable source of various molecules that have antibacterial and anticancer activity. In this study, ten endosymbiotic bacteria of aphids, aphid predators and ants were isolated. Bacterial strains were identified according to the 16S rRNA gene. Ethyl acetate fractions [...] Read more.

Bacterial secondary metabolites are a valuable source of various molecules that have antibacterial and anticancer activity. In this study, ten endosymbiotic bacteria of aphids, aphid predators and ants were isolated. Bacterial strains were identified according to the 16S rRNA gene. Ethyl acetate fractions of methanol extract (EA-ME) were prepared from each isolated bacterium and tested for their antibacterial activities using the disk diffusion method. The EA-ME of three bacterial species, Planococcus sp., Klebsiella aerogenes, Enterococcus avium, from the pomegranate aphids Aphis punicae, Chrysoperia carnea, and Tapinoma magnum, respectively, exhibited elevated antibacterial activity against one or several of the five pathogenic bacteria tested. The inhibition zones ranged from 10.00 ± 0.13 to 20.00 ± 1.11 mm, with minimum inhibitory concentration (MIC) values ranging from 0.156 mg/mL to 1.25 mg/mL. The most notable antibacterial activity was found in the EA-ME of K. aerogenes against Klebsiella pneumonia and Escherichia coli, with an MIC value of 0.156 mg/mL. The cytotoxic activity of EA-ME was dependent on the cell line tested. The most significant cytotoxicity effect was observed for extracts of K. aerogenes and E. avium, at 12.5 µg/mL, against the epithelial cells of lung carcinoma (A549), with a cell reduction of 79.4% and 67.2%, respectively. For the EA-ME of K. aerogenes and Pantoea agglomerans at 12.5 µg/mL, 69.4% and 67.8% cell reduction were observed against human colon cancer (Hct116), respectively. Gas chromatography–mass spectrometry (GC-MS) analysis of three EA-ME revealed the presence of several bioactive secondary metabolites that have been reported previously to possess antibacterial and anticancer properties. To the best of our knowledge, this is the first study to examine the biological activities of endosymbiotic bacteria in aphids, aphid predators and ants. The promising data presented in this study may pave the way for alternative drugs to overcome the continued emergence of multidrug-resistant bacteria, and find alternative drugs to conventional cancer therapies. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products-2nd Edition)

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14 pages, 2812 KiB

Open AccessArticle

The First Phytochemical Investigation of Artemisia divaricate: Sesquiterpenes and Their Anti-Inflammatory Activity

by Siqi Yan, Changqiang Ke, Zheling Feng, Chunping Tang and Yang Ye

Molecules 2023, 28(10), 4254; https://doi.org/10.3390/molecules28104254 - 22 May 2023

Viewed by 1082

Abstract

Artemisia divaricate belongs to the Artemisia genus of the family of Compositae, a sort of perennial herb endemic in most regions of China. For the first time, a phytochemical investigation was carried out on the whole plant of Artemisia divaricate, resulting in [...] Read more.

Artemisia divaricate belongs to the Artemisia genus of the family of Compositae, a sort of perennial herb endemic in most regions of China. For the first time, a phytochemical investigation was carried out on the whole plant of Artemisia divaricate, resulting in the identification of 39 sesquiterpenes, with 9 of them being new (1–9). The structures of the new compounds were fully established using extensive analysis of MS and 1D and 2D NMR spectroscopic data and density functional theory (DFT) NMR calculations. Their structures involve germacrane, eudesmane, and bisabolane types. All the new isolates were evaluated for their anti-inflammatory activities in lipopolysaccharide (LPS)-stimulated murine macrophages of RAW 264.7 cells. Compounds 2 and 8 showed a significant inhibition effect on NO production, with IC₅₀ values of 5.35 ± 0.75 and 7.68 ± 0.54 µM, respectively. Full article

(This article belongs to the Special Issue Chemicals of Natural Origin and Their Biological Activities)

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18 pages, 5032 KiB

Open AccessArticle

Structural Quantification of the Surface-Confined Metal-Organic Precursors Simulated with the Lattice Monte Carlo Method

by Jakub Lisiecki and Paweł Szabelski

Molecules 2023, 28(10), 4253; https://doi.org/10.3390/molecules28104253 - 22 May 2023

Cited by 1 | Viewed by 1063

Abstract

The diversity of surface-confined metal-organic precursor structures, which recently have been observed experimentally, poses a question of how the individual properties of a molecular building block determine those of the resulting superstructure. To answer this question, we use the Monte Carlo simulation technique [...] Read more.

The diversity of surface-confined metal-organic precursor structures, which recently have been observed experimentally, poses a question of how the individual properties of a molecular building block determine those of the resulting superstructure. To answer this question, we use the Monte Carlo simulation technique to model the self-assembly of metal-organic precursors that precede the covalent polymerization of halogenated PAH isomers. For this purpose, a few representative examples of low-dimensional constructs were studied, and their basic structural features were quantified using such descriptors as the orientational order parameter, radial distribution function, and one- and two-dimensional structure factors. The obtained results demonstrated that the morphology of the precursor (and thus the subsequent polymer) could be effectively tuned by a suitable choice of molecular parameters, including size, shape, and intramolecular distribution of halogen substituents. Moreover, our theoretical investigations showed the effect of the main structural features of the precursors on the related indirect characteristics of these constructs. The results reported herein can be helpful in the custom designing and characterization of low-dimensional polymers with adjustable properties. Full article

(This article belongs to the Special Issue Exclusive Feature Papers in Physical Chemistry)

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38 pages, 13790 KiB

Open AccessReview

Recent Progress in the Rational Design of Biothiol-Responsive Fluorescent Probes

by Wenzhi Xie, Jinyu Jiang, Dunji Shu, Yanjun Zhang, Sheng Yang and Kai Zhang

Molecules 2023, 28(10), 4252; https://doi.org/10.3390/molecules28104252 - 22 May 2023

Cited by 4 | Viewed by 1999

Abstract

Biothiols such as cysteine, homocysteine, and glutathione play significant roles in important biological activities, and their abnormal concentrations have been found to be closely associated with certain diseases, making their detection a critical task. To this end, fluorescent probes have become increasingly popular [...] Read more.

Biothiols such as cysteine, homocysteine, and glutathione play significant roles in important biological activities, and their abnormal concentrations have been found to be closely associated with certain diseases, making their detection a critical task. To this end, fluorescent probes have become increasingly popular due to their numerous advantages, including easy handling, desirable spatiotemporal resolution, high sensitivity, fast response, and favorable biocompatibility. As a result, intensive research has been conducted to create fluorescent probes for the detection and imaging of biothiols. This brief review summarizes recent advances in the field of biothiol-responsive fluorescent probes, with an emphasis on rational probe design, including the reaction mechanism, discriminating detection, reversible detection, and specific detection. Furthermore, the challenges and prospects of fluorescence probes for biothiols are also outlined. Full article

(This article belongs to the Special Issue Functionalized Inorganic and Organic Materials: Applications in Sensing, Diagnosis and Pharmaceutics)

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11 pages, 2368 KiB

Open AccessArticle

Synthesis of meta-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions

by Itaru Nakamura, Mai Tachibana, Riku Konta, Hiroki Tashiro and Masahiro Terada

Molecules 2023, 28(10), 4251; https://doi.org/10.3390/molecules28104251 - 22 May 2023

Cited by 1 | Viewed by 1417

Abstract

Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF₆ afforded the corresponding meta-aminophenol derivatives in good to high yields. These reactions proceed via a [1,3]-rearrangement, in which the alkoxy group migrates from the [...] Read more.

Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF₆ afforded the corresponding meta-aminophenol derivatives in good to high yields. These reactions proceed via a [1,3]-rearrangement, in which the alkoxy group migrates from the nitrogen atom to the methyl-substituted ortho position, followed by an oxa-Michael reaction of the resulting ortho-quinol imine intermediate. Full article

(This article belongs to the Special Issue Advances on the Application of N-O Bond Compounds)

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13 pages, 3901 KiB

Open AccessArticle

The Fate of the Chlorophyll Derivatives in Olives Preserved and/or Packaged in Presence of Exogenous Copper

by Fausta Natella, Gianni Pastore, Altero Aguzzi, Paolo Gabrielli, Nicoletta Nardo and Roberto Ambra

Molecules 2023, 28(10), 4250; https://doi.org/10.3390/molecules28104250 - 22 May 2023

Cited by 2 | Viewed by 960

Abstract

Chlorophyll pigments are thought to be responsible for the highly appreciated green color of unfermented Castelvetrano-style table olives, but no studies have considered the effects of a controlled addition of copper during storage or packaging at the industrial level. For this purpose, chlorophyll [...] Read more.

Chlorophyll pigments are thought to be responsible for the highly appreciated green color of unfermented Castelvetrano-style table olives, but no studies have considered the effects of a controlled addition of copper during storage or packaging at the industrial level. For this purpose, chlorophyll derivatives were analyzed in Nocellara cultivar table olives debittered industrially using the Castelvetrano method, via means of HPLC and MS analyses, following the addition of copper in alkaline brines stored at 4 °C for 3 months in 220 L barrels, and during the subsequent storage in acid brines in commercial 400 g packages at 4 °C for up to 18 months. The presence of copper in storage or in packaging brines both contributed significantly to maintaining the green color of the olives, which was associated with a specific pattern of chlorophyll derivatives, as evidenced by principal component analysis. Notably, re-greening was rapidly achievable also for olives that had yellowed for 18 months at a copper concentration below the limit of EU legislation. Finally, by means of PCA, we also demonstrated that a short-term thermic treatment can work as an accelerated predictive tool in determining the fate of chlorophyll derivatives. Full article

(This article belongs to the Special Issue Feature Papers in Food Chemistry—2nd Edition)

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36 pages, 13691 KiB

Open AccessReview

Radical Decarboxylative Carbon–Nitrogen Bond Formation

by Xiangting Li, Xiaobin Yuan, Jiahao Hu, Yajun Li and Hongli Bao

Molecules 2023, 28(10), 4249; https://doi.org/10.3390/molecules28104249 - 22 May 2023

Cited by 5 | Viewed by 2284

Abstract

The carbon–nitrogen bond is one of the most prevalent chemical bonds in natural and artificial molecules, as many naturally existing organic molecules, pharmaceuticals, agrochemicals, and functional materials contain at least one nitrogen atom. Radical decarboxylative carbon–nitrogen bond formation from readily available carboxylic acids [...] Read more.

The carbon–nitrogen bond is one of the most prevalent chemical bonds in natural and artificial molecules, as many naturally existing organic molecules, pharmaceuticals, agrochemicals, and functional materials contain at least one nitrogen atom. Radical decarboxylative carbon–nitrogen bond formation from readily available carboxylic acids and their derivatives has emerged as an attractive and valuable tool in modern synthetic chemistry. The promising achievements in this research topic have been demonstrated via utilizing this strategy in the synthesis of complex natural products. In this review, we will cover carbon–nitrogen bond formation via radical decarboxylation of carboxylic acids, Barton esters, MPDOC esters, N–hydroxyphthalimide esters (NHP esters), oxime esters, aryliodine(III) dicarboxylates, and others, respectively. This review aims to bring readers a comprehensive survey of the development in this rapidly expanding field. We hope that this review will emphasize the knowledge, highlight the proposed mechanisms, and further disclose the fascinating features in modern synthetic applications. Full article

(This article belongs to the Section Organic Chemistry)

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15 pages, 2442 KiB

Open AccessArticle

Detection of Hazelnut and Almond Adulteration in Olive Oil: An Approach by qPCR

by Sonia Ramos-Gómez, María D. Busto and Natividad Ortega

Molecules 2023, 28(10), 4248; https://doi.org/10.3390/molecules28104248 - 22 May 2023

Cited by 1 | Viewed by 1397

Abstract

Virgin olive oil (VOO), characterized by its unique aroma, flavor, and health benefits, is subject to adulteration with the addition of oils obtained from other edible species. The consumption of adulterated olive oil with nut species, such as hazelnut or almond, leads to [...] Read more.

Virgin olive oil (VOO), characterized by its unique aroma, flavor, and health benefits, is subject to adulteration with the addition of oils obtained from other edible species. The consumption of adulterated olive oil with nut species, such as hazelnut or almond, leads to health and safety issues for consumers, due to their high allergenic potential. To detect almond and hazelnut in olive oil, several amplification systems have been analyzed by qPCR assay with a SYBR Green post-PCR melting curve analysis. The systems selected were Cora1F2/R2 and Madl, targeting the genes coding the allergenic protein Cor a 1 (hazelnut) and Pru av 1 (almond), respectively. These primers revealed adequate specificity for each of the targeted species. In addition, the result obtained demonstrated that this methodology can be used to detect olive oil adulteration with up to 5% of hazelnut or almond oil by a single qPCR assay, and with a level as low as 2.5% by a nested-qPCR assay. Thus, the present research has shown that the SYBR-based qPCR assay can be a rapid, precise, and accurate method to detect adulteration in olive oil. Full article

(This article belongs to the Special Issue Virgin Olive Oil: Processing, Byproducts, Quality Control, and Nutraceutical Profile)

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19 pages, 2022 KiB

Open AccessArticle

Effect of Heating Temperature of High-Quality Arbequina, Picual, Manzanilla and Cornicabra Olive Oils on Changes in Nutritional Indices of Lipid, Tocopherol Content and Triacylglycerol Polymerization Process

by Dominik Kmiecik, Monika Fedko, Justyna Małecka, Aleksander Siger and Przemysław Łukasz Kowalczewski

Molecules 2023, 28(10), 4247; https://doi.org/10.3390/molecules28104247 - 22 May 2023

Cited by 2 | Viewed by 2049

Abstract

The aim of the study was to determine the stability and heat resistance of extra premium olive oil. The study material consisted of six extra virgin olive oils (EVOO) obtained from Spain. Four samples were single-strain olive oils: Arbequina, Picual, Manzanilla, and Cornicabra. [...] Read more.

The aim of the study was to determine the stability and heat resistance of extra premium olive oil. The study material consisted of six extra virgin olive oils (EVOO) obtained from Spain. Four samples were single-strain olive oils: Arbequina, Picual, Manzanilla, and Cornicabra. Two samples were a coupage of Arbequina and Picual varieties: Armonia (70% Arbequina and 30% Picual) and Sensation (70% Picual and 30% Arbequina). Olive oil samples were heated at 170 °C and 200 °C in a pan (thin layer model). In all samples, changes in indexes of lipid nutritional quality (PUFA/SFA, index of atherogenicity, index of thrombogenicity, and hypocholesterolemic/hypercholesterolemic ratio), changes in tocopherol, total polar compounds content, and triacylglycerol polymers were determined. Heating olive oil in a thin layer led to its degradation and depended on the temperature and the type of olive oil. Increasing the temperature from 170 to 200 °C resulted in significantly higher degradation of olive oil. At 200 °C, deterioration of lipid nutritional indices, total tocopherol degradation, and formation of triacylglycerol polymers were observed. A twofold increase in the polar fraction was also observed compared to samples heated at 170 °C. The most stable olive oils were Cornicabra and Picual. Full article

(This article belongs to the Special Issue Virgin Olive Oil: Processing, Byproducts, Quality Control, and Nutraceutical Profile)

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37 pages, 8426 KiB

Open AccessReview

A Review of Research Progress on the Performance of Intelligent Polymer Gel

by Shuangchun Yang, Zhenye Liu, Yi Pan, Jian Guan, Peng Yang and Muratbekova Asel

Molecules 2023, 28(10), 4246; https://doi.org/10.3390/molecules28104246 - 22 May 2023

Cited by 1 | Viewed by 1404

Abstract

Intelligent polymer gel, as a popular polymer material, has been attracting much attention for its application. An intelligent polymer gel will make corresponding changes to adapt to the environment after receiving stimuli; therefore, an intelligent polymer gel can play its role in many [...] Read more.

Intelligent polymer gel, as a popular polymer material, has been attracting much attention for its application. An intelligent polymer gel will make corresponding changes to adapt to the environment after receiving stimuli; therefore, an intelligent polymer gel can play its role in many fields. With the research on intelligent polymer gels, there is great potential for applications in the fields of drug engineering, molecular devices, and biomedicine in particular. The strength and responsiveness of the gels can be improved under different configurations in different technologies to meet the needs in these fields. There is no discussion on the application of intelligent polymer gels in these fields; therefore, this paper reviews the research progress of intelligent polymer gel, describes the important research of some intelligent polymer gel, summarizes the research progress and current situation of intelligent polymer gel in the environment of external stimulation, and discusses the performance and future development direction of intelligent polymer gel. Full article

(This article belongs to the Special Issue Smart Polymeric Micro/Nanomaterials)

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17 pages, 6818 KiB

Open AccessArticle

Efficient Conversion of Lignin to Aromatics via Catalytic Fast Pyrolysis over Niobium-Doped HZSM-5

by Zhen Li, Huihui Zhang, Deshi Yang, Zhipeng Hu, Fengqiang Wang and Zhijun Zhang

Molecules 2023, 28(10), 4245; https://doi.org/10.3390/molecules28104245 - 22 May 2023

Cited by 3 | Viewed by 1361

Abstract

A niobium-doped HZSM-5 (H[Nb]ZSM-5) was prepared by a hydrothermal synthesis method. The morphology, phase structure, composition, pore structure, and acid content of the catalyst were characterized using a series of analysis techniques such as scanning electron microscope (SEM), energy-dispersive X-ray (EDX), X-ray diffraction [...] Read more.

A niobium-doped HZSM-5 (H[Nb]ZSM-5) was prepared by a hydrothermal synthesis method. The morphology, phase structure, composition, pore structure, and acid content of the catalyst were characterized using a series of analysis techniques such as scanning electron microscope (SEM), energy-dispersive X-ray (EDX), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), nitrogen adsorption-desorption, and temperature programmed desorption measurements (NH₃-TPD). The H[Nb]ZSM-5 catalyst fully remained within the crystal framework and pore structure of HZSM-5. Meanwhile, introduction of niobium (V) endowed the catalyst with both Lewis acid and Bronsted acid sites. Catalytic fast pyrolysis (CFP) of alkali lignin was carried out through a pyrolysis and gas chromatography-mass spectrometry (Py-GC/MS) at 650 °C and atmospheric pressure. The results indicated that H[Nb]ZSM-5 can efficiently and selectively convert lignin into monoaromatic hydrocarbons (MAHs), compared to the control HZSM-5. Catalyzed by H[Nb]ZSM-5, the content of MAHs and aliphatic hydrocarbons reached 43.4% and 20.8%, respectively; while under the catalysis of HZSM-5, these values were 35.5% and 3.2%, respectively. H[Nb]ZSM-5 remarkably lowered the phenol content to approximately 2.8%, which is far lower than the content (24.9%) obtained under HZSM-5 catalysis. Full article

(This article belongs to the Collection Recycling of Biomass Resources: Biofuels and Biochemicals)

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17 pages, 3953 KiB

Open AccessArticle

p-Synephrine Indicates Internal Maturity of Citrus grandis (L.) Osbeck cv. Mato Peiyu—Reclaiming Functional Constituents from Nonedible Parts

by Li-Yun Lin, Chiung Chi Peng, Yi-Ping Huang, Kuan-Chou Chen and Robert Y. Peng

Molecules 2023, 28(10), 4244; https://doi.org/10.3390/molecules28104244 - 22 May 2023

Viewed by 1178

Abstract

The processing of Citrus grandis Osbeck cv. Mato Peiyu (CGMP) fruits generates a considerable amount of waste, mainly the flavedo, albedo, and segment membrane; the generated waste yields severe environmental and economic challenges. In this study, we tried to reclaim some functional chemicals [...] Read more.

The processing of Citrus grandis Osbeck cv. Mato Peiyu (CGMP) fruits generates a considerable amount of waste, mainly the flavedo, albedo, and segment membrane; the generated waste yields severe environmental and economic challenges. In this study, we tried to reclaim some functional chemicals from the waste. Our data indicated that the essential oil content in the flavedo was 0.76–1.34%, with the major component being monoterpenes (93.75% in August, declining to 85.56% in November, including mainly limonene (87.08% to 81.12%) and others such as β-myrcene). p-Synephrine (mg/100 g dry weight) declined accordingly (flavedo, 10.40 to 2.00; albedo, 1.80 to 0.25; segment membrane, 0.3 in August, 0.2 in September, and none since October). Polyphenols (in μg/g) included gallic acid (70.32–110.25, 99.27–252.89, and 105.78–187.36, respectively); protocatechuic acid (65.32–204.94, 26.35–72.35, and 214.98–302.65, respectively), p-coumaric acid (30.63–169.13, 4.32–17.00, and 6.68–34.32, respectively), ferulic acid (12.36–39.36, 1.21–10.25, and 17.07–39.63, respectively), and chlorogenic acid (59.19–199.36, 33.08–108.57, and 65.32–150.14, respectively). Flavonoids (in μg/g) included naringin (flavedo, 89.32–283.19), quercetin (181.05–248.51), nobiletin (259.75–563.7), hesperidin, and diosmin. The phytosterol content (mg/100 g) was 12.50–44.00 in the flavedo. The total dietary fiber in the segment membrane was 57 g/100 g. The antioxidant activity against the DPPH^• and ABTS^+• free radicals was moderately high. In conclusion, the waste of CGMP fruits is worth reclaiming for essential oil, p-synephrine, polyphenolics, and dietary fiber. Notably, p-synephrine content (flavedo: <8 mg/100 g dry weight, albedo: <2.0, or segment membrane: <0.4 mg) can serve as a marker of the internal maturation of CGMP fruits. Full article

(This article belongs to the Special Issue Biosynthesis and Metabolism of Bioactive Components in Fruits and Vegetables)

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20 pages, 1464 KiB

Open AccessReview

Application of Rosmarinic Acid with Its Derivatives in the Treatment of Microbial Pathogens

by Ourdia-Nouara Kernou, Zahra Azzouz, Khodir Madani and Patricia Rijo

Molecules 2023, 28(10), 4243; https://doi.org/10.3390/molecules28104243 - 22 May 2023

Cited by 8 | Viewed by 1997

Abstract

The emergence of the antimicrobial resistance phenomena on and the harmful consequences of the use of antibiotics motivate the necessity of innovative antimicrobial therapies, while natural substances are considered a promising alternative. Rosmarin is an original plant compound listed among the hydroxycinnamic acids. [...] Read more.

The emergence of the antimicrobial resistance phenomena on and the harmful consequences of the use of antibiotics motivate the necessity of innovative antimicrobial therapies, while natural substances are considered a promising alternative. Rosmarin is an original plant compound listed among the hydroxycinnamic acids. This substance has been widely used to fight microbial pathology and chronic infections from microorganisms like bacteria, fungi and viruses. Also, various derivatives of rosmarinic acid, such as the propyl ester of rosmarinic acid, rosmarinic acid methyl ester or the hexyl ester of rosmarinic acid, have been synthesized chemically, which have been isolated as natural antimicrobial agents. Rosmarinic acid and its derivatives were combined with antibiotics to obtain a synergistic effect. This review reports on the antimicrobial effects of rosmarinic acid and its associated derivatives, both in their free form and in combination with other microbial pathogens, and mechanisms of action. Full article

(This article belongs to the Special Issue Drug Development Inspired by Natural Products II)

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10 pages, 3287 KiB

Open AccessArticle

Cocrystallization of Progesterone with Nitrogen Heterocyclic Compounds: Synthesis, Characterization, Calculation and Property Evaluation

by Juan Xu, Wei Gao, Qi Zhang and Lifeng Ning

Molecules 2023, 28(10), 4242; https://doi.org/10.3390/molecules28104242 - 22 May 2023

Viewed by 1017

Abstract

Progesterone injection is oily because of its poor solubility. It is necessary to develop new dosage forms or delivery methods for Progesterone. Six cocrystals of Progesterone with nitrogen heterocyclic compounds (2,6-diaminopyridine, isonicotinamide, 4-aminopyridine, aminopyrazine, picolinamide and pyrazinamide) have been designed and prepared by [...] Read more.

Progesterone injection is oily because of its poor solubility. It is necessary to develop new dosage forms or delivery methods for Progesterone. Six cocrystals of Progesterone with nitrogen heterocyclic compounds (2,6-diaminopyridine, isonicotinamide, 4-aminopyridine, aminopyrazine, picolinamide and pyrazinamide) have been designed and prepared by ethyl acetate-assisted grinding, of which four cocrystals (2,6-diaminopyridine, isonicotinamide, 4-aminopyridine and aminopyrazine) had single crystal data in 1:1 stoichiometry. Metadynamics-genetic crossing was used to search and optimize various cluster structures to explain the reason the other two cocrystals could not be obtained with suitable size for single crystal X-ray diffraction. In contrast to the carboxyl group, the amide group and amino group were good substituents in the pyridine/pyrazine ring for cocrystallization with Progesterone, which meant inductive effect played an important role in nitrogen heterocyclic compounds containing reactive hydrogen. All cocrystals were more soluble than Progesterone in water, and Progesterone–pyrazinamide cocystal featured the best water solubility performance with an approximately six-fold increase over free Progesterone. This successful attempt provides an effective route for designing and manufacturing novel solid states of Progesterone. Full article

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15 pages, 4902 KiB

Open AccessArticle

Leocarpinolide B Attenuates Collagen Type II-Induced Arthritis by Inhibiting DNA Binding Activity of NF-κB

by Ke-Gang Linghu, Guan-Ding Zhao, Dai-Yan Zhang, Shi-Hang Xiong, Guo-Ping Wu, Li-Yu Shen, Wen-Qing Cui, Tian Zhang, Yuan-Jia Hu, Bing Guo, Xiang-Chun Shen and Hua Yu

Molecules 2023, 28(10), 4241; https://doi.org/10.3390/molecules28104241 - 22 May 2023

Cited by 1 | Viewed by 1582

Abstract

Rheumatoid arthritis (RA) is a chronic autoimmune disease triggered by a cascading inflammatory response. Sigesbeckia Herba (SH) has long been utilized as a traditional remedy to alleviate symptoms associated with rheumatism. Our previous study found that leocarpinolide B (LB), a sesquiterpene lactone isolated [...] Read more.

Rheumatoid arthritis (RA) is a chronic autoimmune disease triggered by a cascading inflammatory response. Sigesbeckia Herba (SH) has long been utilized as a traditional remedy to alleviate symptoms associated with rheumatism. Our previous study found that leocarpinolide B (LB), a sesquiterpene lactone isolated from the whole plant of SH, possesses potent a anti-inflammatory effect on macrophages. This study was designed to evaluate the therapeutic effects of LB on RA, and further investigate the underlying mechanisms. In collagen type II-induced arthritic mice, LB was demonstrated to decrease the production of autoimmune antibodies in serum and inflammatory cytokines in the joint muscles and recover the decreased regulatory T lymphocytes in spleen. Moreover, LB significantly suppressed the inflammatory infiltration, formation of pannus and bone erosion in the paw joints. In vitro testing showed that LB inhibited the proliferation, migration, invasion, and secretion of inflammatory cytokines in IL-1β-induced human synovial SW982 cells. Network pharmacology and molecular docking suggested NF-κB p65 could be the potential target of LB on RA treatment, subsequent experimental investigation confirmed that LB directly interacted with NF-κB p65 and reduced the DNA binding activity of NF-κB in synovial cells. In conclusion, LB significantly attenuated the collagen type II-induced arthritis, which was at least involved in the inhibition of DNA binding activity of NF-κB through a direct binding to NF-κB p65. These findings suggest that LB could be a valuable lead compound for developing anti-RA drugs. Full article

(This article belongs to the Special Issue Novel Therapeutic Targets and Potential Drugs for Inflammatory Disease)

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25 pages, 3767 KiB

Open AccessArticle

Novel Thiazolylketenyl Quinazolinones as Potential Anti-MRSA Agents and Allosteric Modulator for PBP2a

by Jie Dai, Narsaiah Battini, Zhonglin Zang, Yan Luo and Chenghe Zhou

Molecules 2023, 28(10), 4240; https://doi.org/10.3390/molecules28104240 - 22 May 2023

Cited by 7 | Viewed by 1388

Abstract

Bacterial infections caused by methicillin-resistant Staphylococcus aureus have seriously threatened public health. There is an urgent need to propose an existing regimen to overcome multidrug resistance of MRSA. A unique class of novel anti-MRSA thiazolylketenyl quinazolinones (TQs) and their analogs were developed. Some synthesized [...] Read more.

Bacterial infections caused by methicillin-resistant Staphylococcus aureus have seriously threatened public health. There is an urgent need to propose an existing regimen to overcome multidrug resistance of MRSA. A unique class of novel anti-MRSA thiazolylketenyl quinazolinones (TQs) and their analogs were developed. Some synthesized compounds showed good bacteriostatic potency. Especially TQ 4 was found to exhibit excellent inhibition against MRSA with a low MIC of 0.5 μg/mL, which was 8-fold more effective than norfloxacin. The combination of TQ 4 with cefdinir showed stronger antibacterial potency. Further investigation revealed that TQ 4, with low hemolytic toxicity and low drug resistance, was not only able to inhibit biofilm formation but also could reduce MRSA metabolic activity and showed good drug-likeness. Mechanistic explorations revealed that TQ 4 could cause leakage of proteins by disrupting membrane integrity and block DNA replication by intercalated DNA. Furthermore, the synergistic antibacterial effect with cefdinir might be attributed to TQ 4 with the ability to induce PBP2a allosteric regulation of MRSA and further trigger the opening of the active site to promote the binding of cefdinir to the active site, thus inhibiting the expression of PBP2a, thereby overcoming MRSA resistance and significantly enhancing the anti-MRSA activity of cefdinir. A new strategy provided by these findings was that TQ 4, possessing both excellent anti-MRSA activity and allosteric effect of PBP2a, merited further development as a novel class of antibacterial agents to overcome increasingly severe MRSA infections. Full article

(This article belongs to the Special Issue Biological Activity of Natural and Synthetic Compounds 2.0)

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23 pages, 441 KiB

Open AccessReview

The Genus Capsicum: A Review of Bioactive Properties of Its Polyphenolic and Capsaicinoid Composition

by Rodrigo Alonso-Villegas, Rosa María González-Amaro, Claudia Yuritzi Figueroa-Hernández and Ingrid Mayanin Rodríguez-Buenfil

Molecules 2023, 28(10), 4239; https://doi.org/10.3390/molecules28104239 - 22 May 2023

Cited by 5 | Viewed by 2256

Abstract

Chili is one of the world’s most widely used horticultural products. Many dishes around the world are prepared using this fruit. The chili belongs to the genus Capsicum and is part of the Solanaceae family. This fruit has essential biomolecules such as carbohydrates, [...] Read more.

Chili is one of the world’s most widely used horticultural products. Many dishes around the world are prepared using this fruit. The chili belongs to the genus Capsicum and is part of the Solanaceae family. This fruit has essential biomolecules such as carbohydrates, dietary fiber, proteins, and lipids. In addition, chili has other compounds that may exert some biological activity (bioactivities). Recently, many studies have demonstrated the biological activity of phenolic compounds, carotenoids, and capsaicinoids in different varieties of chili. Among all these bioactive compounds, polyphenols are one of the most studied. The main bioactivities attributed to polyphenols are antioxidant, antimicrobial, antihyperglycemic, anti-inflammatory, and antihypertensive. This review describes the data from in vivo and in vitro bioactivities attributed to polyphenols and capsaicinoids of the different chili products. Such data help formulate functional foods or food ingredients. Full article

(This article belongs to the Special Issue Biological Activity of Phenolics and Polyphenols in Nature Products)

12 pages, 2364 KiB

Open AccessArticle

Exploring Echinops polyceras Boiss. from Jordan: Essential Oil Composition, COX, Protein Denaturation Inhibitory Power and Antimicrobial Activity of the Alcoholic Extract

by Hazem S. Hasan, Ashok K. Shakya, Hala I. Al-Jaber, Hana E. Abu-Sal and Lina M. Barhoumi

Molecules 2023, 28(10), 4238; https://doi.org/10.3390/molecules28104238 - 22 May 2023

Cited by 1 | Viewed by 1256

Abstract

In this article, we present the first detailed analysis of the hydro-distilled essential oil (HDEO) of the inflorescence heads of Echinops polyceras Boiss. (Asteraceae) from the flora of Jordan, offering observations at different growth (pre-flowering, full-flowering and post-flowering) stages. Additionally, we investigated the [...] Read more.

In this article, we present the first detailed analysis of the hydro-distilled essential oil (HDEO) of the inflorescence heads of Echinops polyceras Boiss. (Asteraceae) from the flora of Jordan, offering observations at different growth (pre-flowering, full-flowering and post-flowering) stages. Additionally, we investigated the methanolic extract obtained from the aerial parts of the plant material at the full flowering stage in order to determine its inhibitory activity in terms of COX and protein denaturation and evaluate its antimicrobial effects against S. aureus (Gram-positive) and E. coli (Gram-negative) bacteria. Performing GC/MS analysis of HDEO, obtained from the fresh inflorescence heads at the different growth stages, resulted in the identification of 192 constituents. The main class of compounds detected in these three stages comprised aliphatic hydrocarbons and their derivatives, which amounted to 50.04% (pre-flower), 40.28% (full-flower) and 41.34% (post-flower) of the total composition. The oils also contained appreciable amounts of oxygenated terpenoids, primarily sesquiterpenoids and diterpenoids. The pre-flowering stage was dominated by (2E)-hexenal (8.03%) in addition to the oxygenated diterpene (6E,10E)-pseudo phytol (7.54%). The full-flowering stage primarily contained (6E,10E)-pseudo phytol (7.84%), β-bisabolene (7.53%, SH) and the diterpene hydrocarbon dolabradiene (5.50%). The major constituents detected in the HDEO obtained at the post-flowering stage included the oxygenated sesquiterpenoid intermedeol (5.53%), the sesquiterpene hydrocarbon (E)-caryophyllene (5.01%) and (6E,10E)-pseudo phytol (4.47%). The methanolic extract obtained from air-dried aerial parts of E. polyceras displayed more COX-2 inhibition than COX-1 inhibition at a concentration level of 200 µg/mL. The extract exhibited a capacity to inhibit protein denaturation that was comparable with respect to the activity of diclofenac sodium and displayed moderate levels of antimicrobial activity against both bacterial species. The current results demonstrate the need to perform further detailed phytochemical investigations to isolate and characterize active constituents. Full article

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16 pages, 3676 KiB

Open AccessArticle

Photosensitive Dye as an Ideal Peroxymonosulfate Activator for Efficient Self-Degradation: A Novel Idea of Using Waste to Treat Waste

by Zhiyao Zhang, Zhaolin Li, Xue Bai, Juan Shi, Min Hu, Jin Chai, Keqian Li and Pengkang Jin

Molecules 2023, 28(10), 4237; https://doi.org/10.3390/molecules28104237 - 22 May 2023

Cited by 2 | Viewed by 1042

Abstract

Commonly used peroxydisulfate (PS) or peroxymonosulfate (PMS) activation methods have been limited in their practical application due to certain drawbacks, such as high cost, high energy consumption and secondary pollution. In this study, a catalyst-free alizarin green (AG) self-activating PMS catalytic system was [...] Read more.

Commonly used peroxydisulfate (PS) or peroxymonosulfate (PMS) activation methods have been limited in their practical application due to certain drawbacks, such as high cost, high energy consumption and secondary pollution. In this study, a catalyst-free alizarin green (AG) self-activating PMS catalytic system was constructed based on photosensitization properties of dye, which ultimately achieved efficient degradation of the dye activator, also the target pollutant. Here, 52.5% of the 100 mL mixture of 10 mg/L AG decomposed within 60 min with 1 mM PMS under visible-light irradiation, thereby showing a strong pH adaptation. Mechanism of AG self-activating PMS was revealed that the photo-excited AG can effectively transfer photo-induced electrons to PMS for its activation, which generates reactive oxidizing species dominated by singlet oxygen (¹O₂), and supplemented by hydroxyl radical (•OH), superoxide radical (O₂^•−) and sulfate radical (SO₄^•−) to realize the efficient self-degradation of the dye pollutants. Moreover, such self-catalytic system operated well under natural sunlight irradiation, indicating the great application potential in the actual wastewater treatment. Herein, photosensitive dye acted as an ideal PMS activator realizing its efficient self-degradation, which provides a novel idea of “using waste to treat waste” for developing wastewater treatment process in a high-efficiency and low-consumption way. Full article

(This article belongs to the Special Issue Energy-Relevant Advanced Materials)

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10 pages, 1532 KiB

Open AccessArticle

A Quick Method to Synthesize Extrachromosomal Circular DNA In Vitro

by Shanru Zuo, Xueguang Li, Yide Yang, Junhua Zhou and Quanyuan He

Molecules 2023, 28(10), 4236; https://doi.org/10.3390/molecules28104236 - 22 May 2023

Viewed by 1876

Abstract

Extrachromosomal circular DNA (eccDNA) is a special class of circular DNA in eukaryotes. Recent studies have suggested that eccDNA is the product of genomic instability and has important biological functions to regulate many downstream biological processes. While NGS (Next-Generation Sequencing)-based eccDNA sequencing has [...] Read more.

Extrachromosomal circular DNA (eccDNA) is a special class of circular DNA in eukaryotes. Recent studies have suggested that eccDNA is the product of genomic instability and has important biological functions to regulate many downstream biological processes. While NGS (Next-Generation Sequencing)-based eccDNA sequencing has led to the identification of many eccDNAs in both healthy and diseased tissues, the specific biological functions of individual eccDNAs have yet to be clearly elucidated. Synthesizing eccDNAs longer than 1 kb with specific sequences remains a major challenge in the field, which has hindered our ability to fully understand their functions. Current methods for synthesizing eccDNAs primarily rely on chemical oligo synthesis, ligation, or the use of a specific gene editing and recombination systems. Therefore, these methods are often limited by the length of eccDNAs and are complex, expensive, as well as time-consuming. In this study, we introduce a novel method named QuickLAMA (Ligase-Assisted Minicircle Accumulation) for rapidly synthesizing eccDNAs up to 2.6 kb using a simple PCR and ligation approach. To validate the efficacy of our method, we synthesized three eccDNAs of varying lengths from cancer tissue and PC3 cells and confirmed successful circularization through sequencing and restriction enzyme digestion. Additional analyses have demonstrated that this method is highly efficient, cost-effective, and time-efficient, with good reproducibility. Using the method, a well-trained molecular biologist can synthesize and purify multiple eccDNAs within a single day, and it can be easily standardized and processed in a high-throughput manner, indicating the potential of the method to produce a wide range of desired eccDNAs and promote the translation of eccDNA research into clinical applications. Full article

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14 pages, 1399 KiB

Open AccessArticle

Highly-Selective Analytical Strategy for 90 Pesticides and Metabolites Residues in Fish and Shrimp Samples

by Yage Guo, Jun Xie, Fengshou Dong, Xiaohu Wu, Xinglu Pan, Xingang Liu, Yongquan Zheng, Jie Zhang and Jun Xu

Molecules 2023, 28(10), 4235; https://doi.org/10.3390/molecules28104235 - 22 May 2023

Cited by 2 | Viewed by 1310

Abstract

The analysis of pesticide residues in aquatic products is challenging due to low residue levels and the complex matrix interference. In this study, we developed a simple, fast method for the trace analysis of 90 pesticides and metabolites in aquatic products. The analytes [...] Read more.

The analysis of pesticide residues in aquatic products is challenging due to low residue levels and the complex matrix interference. In this study, we developed a simple, fast method for the trace analysis of 90 pesticides and metabolites in aquatic products. The analytes covered a wide polarity range with log Kow (log octanol-water partition coefficient) ranging from −1.2 to 6.37. Grass carp (Ctenopharyngodon idellus) and prawn (Penaeus chinensis) samples were chosen to validate the quantification method. The samples were extracted by 0.2% formic-acetonitrile, cleaned by solid-phase extraction (PRiME HLB), and analyzed by high performance liquid chromatography−tandem mass spectrometry. The results showed good linearities for the analytes and were observed in the range of 0.05–50 μg/L. The recoveries of the method were within 50.4–118.6%, with the relative standard deviations being lower than 20%. The limits of quantifications (LOQs) of the method were in the range of 0.05–5.0 μg/kg, which were superior to values compared with other research. The developed method was applied to detect pesticide residues in prawn samples from eastern coastal areas of China. Three herbicide residues of diuron, prometryn, and atrazine were detected in prawn samples. The method was sensitive and efficient, which is of significance in expanding the screening scope and improving the quantitative analysis efficiency in aquatic products. Full article

(This article belongs to the Section Analytical Chemistry)

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20 pages, 2070 KiB

Open AccessArticle

Synthesis, Pharmacological Evaluation, and Molecular Modeling of Lappaconitine–1,5-Benzodiazepine Hybrids

by Kirill P. Cheremnykh, Arkadiy O. Bryzgalov, Dmitry S. Baev, Sergey A. Borisov, Yulia S. Sotnikova, Victor A. Savelyev, Tatyana G. Tolstikova, Shamansur S. Sagdullaev and Elvira E. Shults

Molecules 2023, 28(10), 4234; https://doi.org/10.3390/molecules28104234 - 22 May 2023

Viewed by 1290

Abstract

Diterpenoid alkaloids, originating from the amination of natural tetracyclic diterpenes, have long interested scientists due to their medicinal uses and infamous toxicity which has limited the clinical application of the native compound. Alkaloid lappaconitine extracted from various Aconitum and Delphinium species has displayed [...] Read more.

Diterpenoid alkaloids, originating from the amination of natural tetracyclic diterpenes, have long interested scientists due to their medicinal uses and infamous toxicity which has limited the clinical application of the native compound. Alkaloid lappaconitine extracted from various Aconitum and Delphinium species has displayed extensive bioactivities and active ongoing research to reduce its adverse effects. A convenient route to construct hybrid molecules containing diterpenoid alkaloid lappaconitine and 3H-1,5-benzodiazepine fragments was proposed. The key stage involved the formation of 5′-alkynone-lappaconitines in situ by acyl Sonogashira coupling of 5′-ethynyllappaconitine, followed by cyclocondensation with o-phenylenediamine. New hybrid compounds showed low toxicity and outstanding analgesic activity in experimental pain models, which depended on the nature of the substituent in the benzodiazepine nucleus. An analogous dependence was also shown for the antiarrhythmic activity in the epinephrine arrhythmia test in vivo. Studies on the isolated atrium have shown that the mechanism of action of the new compounds is included the blockade of beta-adrenergic receptors and potassium channels. Molecular docking analysis was conducted to determine the binding potential of target molecules with the voltage-gated sodium channel NaV1.5. All obtained results provide a basis for future rational modifications of lappaconitine, reducing side effects, while retaining its therapeutic effects. Full article

(This article belongs to the Section Medicinal Chemistry)

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29 pages, 7216 KiB

Open AccessReview

Added Complexity!—Mechanistic Aspects of Heterobimetallic Complexes for Application in Homogeneous Catalysis

by Zeno Fickenscher and Evamarie Hey-Hawkins

Molecules 2023, 28(10), 4233; https://doi.org/10.3390/molecules28104233 - 22 May 2023

Cited by 3 | Viewed by 1651

Abstract

Inspired by multimetallic assemblies and their role in enzyme catalysis, chemists have developed a plethora of heterobimetallic complexes for application in homogeneous catalysis. Starting with small heterobimetallic complexes with σ-donating and π-accepting ligands, such as N-heterocyclic carbene and carbonyl ligands, more and more [...] Read more.

Inspired by multimetallic assemblies and their role in enzyme catalysis, chemists have developed a plethora of heterobimetallic complexes for application in homogeneous catalysis. Starting with small heterobimetallic complexes with σ-donating and π-accepting ligands, such as N-heterocyclic carbene and carbonyl ligands, more and more complex systems have been developed over the past two decades. These systems can show a significant increase in catalytic activity compared with their monometallic counterparts. This increase can be attributed to new reaction pathways enabled by the presence of a second metal center in the active catalyst. This review focuses on mechanistic aspects of heterobimetallic complexes in homogeneous catalysis. Depending on the type of interaction of the second metal with the substrates, heterobimetallic complexes can be subdivided into four classes. Each of these classes is illustrated with multiple examples, showcasing the versatility of both, the types of interactions possible, and the reactions accessible. Full article

(This article belongs to the Topic Catalytic Applications of Transition Metals)

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14 pages, 2079 KiB

Open AccessReview

Honey Quality Control: Review of Methodologies for Determining Entomological Origin

by Saeed Mohamadzade Namin, Sampat Ghosh and Chuleui Jung

Molecules 2023, 28(10), 4232; https://doi.org/10.3390/molecules28104232 - 22 May 2023

Cited by 1 | Viewed by 2070

Abstract

Honey is a widely consumed natural product, and its entomological origin can significantly influence its market value. Therefore, traceability of the entomological origin of honey should also be considered in honey quality control protocols. Although several methods exist, such as physicochemical characterization and [...] Read more.

Honey is a widely consumed natural product, and its entomological origin can significantly influence its market value. Therefore, traceability of the entomological origin of honey should also be considered in honey quality control protocols. Although several methods exist, such as physicochemical characterization and bioactivity profiling of honey of different entomological origins, the most promising three methods for entomological authentication of honey include protein-based identification, chemical profiling, and a DNA-based method. All of these methods can be applied for reliable identification of the entomological origin of honey. However, as the honey is a complex matrix, the inconsistency of the results obtained by these methods is a pragmatic challenge, and therefore, the use of each method in all the cases is questionable. Most of these methodologies can be used for authentication of newly harvested honey and it is worth understanding the possibility of using these methods for authentication of relatively old samples. Most probably, using DNA-based methods targeting small fragments of DNA can provide the best result in old samples, however, the species-specific primers targeting short fragments are limited and not available for all species. Therefore, using universal primers in combination with a DNA metabarcoding approach can be a good solution that requires further investigation. This present article describes the applications of different methods, their pros, and their cons to identify honey based on entomological origin. Full article

(This article belongs to the Special Issue The Chemistry of Honey and Other Bee Products: Novel Applications and Quality)

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17 pages, 3396 KiB

Open AccessArticle

Dextran Methacrylate Reactions with Hydroxyl Radicals and Hydrated Electrons in Water: A Kinetic Study Using Pulse Radiolysis

by Kamila J. Szafulera, Radosław A. Wach and Piotr Ulański

Molecules 2023, 28(10), 4231; https://doi.org/10.3390/molecules28104231 - 22 May 2023

Cited by 2 | Viewed by 1177

Abstract

Dextran methacrylate (Dex-MA) is a biodegradable polysaccharide derivative that can be cross-linked by ionizing radiation. It is therefore considered a potential replacement for synthetic hydrophilic polymers in current radiation technologies used for synthesizing hydrophilic cross-linked polymer structures such as hydrogels, mainly for medical [...] Read more.

Dextran methacrylate (Dex-MA) is a biodegradable polysaccharide derivative that can be cross-linked by ionizing radiation. It is therefore considered a potential replacement for synthetic hydrophilic polymers in current radiation technologies used for synthesizing hydrophilic cross-linked polymer structures such as hydrogels, mainly for medical applications. This work is focused on the initial steps of radiation-induced cross-linking polymerization of Dex-MA in water. Rate constants of two major transient water radiolysis products—hydroxyl radicals (^•OH) and hydrated electrons (

e_{aq}^{-}

)—with various samples of Dex-MA (based on 6–500 kDa dextrans of molar degree of substitution or DS with methacrylate groups up to 0.66) as well as non-substituted dextran were determined by pulse radiolysis with spectrophotometric detection. It has been demonstrated that these rate constants depend on both the molecular weight and DS; reasons for these effects are discussed and reaction mechanisms are proposed. Selected spectral data of the transient species formed by ^•OH- and

e_{aq}^{-}

-induced reactions are used to support the discussion. The kinetic data obtained in this work and their interpretation are expected to be useful for controlled synthesis of polysaccharide-based hydrogels and nanogels of predefined structure and properties. Full article

(This article belongs to the Special Issue Polysaccharide-Based Biopolymer: Recent Development and Applications)

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25 pages, 5133 KiB

Open AccessArticle

The Impact of Fermentation Temperature and Cap Management on Selected Volatile Compounds and Temporal Sensory Characteristics of Grenache Wines from the Central Coast of California

by Emily S. Stoffel, Taylor M. Robertson, Anibal A. Catania and L. Federico Casassa

Molecules 2023, 28(10), 4230; https://doi.org/10.3390/molecules28104230 - 22 May 2023

Viewed by 1631

Abstract

Grenache wines from the Central Coast of California were subjected to different alcoholic fermentation temperature regimes (Cold, Cold/Hot, Hot) and cap management protocols, namely, punch down (PD), or no punch down (No PD), to determine the effect of these practices on the color, [...] Read more.

Grenache wines from the Central Coast of California were subjected to different alcoholic fermentation temperature regimes (Cold, Cold/Hot, Hot) and cap management protocols, namely, punch down (PD), or no punch down (No PD), to determine the effect of these practices on the color, aroma, and the retronasal and mouthfeel sensory characteristics of the resulting wines. Descriptive analysis (n = 8, line scale rating 0–15) results indicated that the combination of a hot fermentation temperature and no punch downs led to a significantly higher intensity in perceived color saturation (7.89) and purple hue (8.62). A two-way analysis of variance (ANOVA) showed that cap management was significantly more impactful on the perception of orthonasal aromas than fermentation temperature. The reduction aroma was significantly higher in No PD wines (5.02) compared to PD wines (3.50), while rose and hot aromas had significantly higher intensity perception for PD wines (5.18, 6.80) than for No PD wines (6.80, 6.14). Conversely, analysis of selected volatile compounds indicated that fermentation temperature was more impactful than cap management regime. Cold/Hot wines had higher concentrations of important esters such as ethyl hexanoate (650 µg/L) and isoamyl acetate (992 µg/L). Cold wines had a higher concentration of β-damascenone (0.719 µg/L). TCATA evaluation (n = 8) indicated that Cold/Hot PD wines had a significantly higher citation proportion of fruit flavor (1.0) and velvet astringency perception (0.80) without significant reduction flavors. Finally, the present study represents a contribution with the main volatile compounds (e.g., β-damascenone and esters in the Cold and Cold/Hot fermented wines, respectively; hexanol in PD wines, which may be potentially responsible for a hot mouthfeel), and sensory characteristics (red fruit, tropical fruit, white pepper, and rose) of Grenache wines grown in the Mediterranean climate of the Central Coast of California. Full article

(This article belongs to the Topic Advances in Analysis of Flavors and Fragrances: Chemistry, Properties and Applications in Food Quality Improvement)

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15 pages, 2466 KiB

Open AccessReview

The History of Desulfovibrio gigas Aldehyde Oxidoreductase—A Personal View

by José J. G. Moura

Molecules 2023, 28(10), 4229; https://doi.org/10.3390/molecules28104229 - 22 May 2023

Cited by 2 | Viewed by 1214

Abstract

A story going back almost 40 years is presented in this manuscript. This is a different and more challenging way of reporting my research and I hope it will be useful to and target a wide-ranging audience. When preparing the manuscript and collecting [...] Read more.

A story going back almost 40 years is presented in this manuscript. This is a different and more challenging way of reporting my research and I hope it will be useful to and target a wide-ranging audience. When preparing the manuscript and collecting references on the subject of this paper—aldehyde oxidoreductase from Desulfovibrio gigas—I felt like I was travelling back in time (and space), bringing together the people that have contributed most to this area of research. I sincerely hope that I can give my collaborators the credit they deserve. This study is not presented as a chronologic narrative but as a grouping of topics, the development of which occurred over many years. Full article

(This article belongs to the Special Issue Molybdenum and Tungsten Enzymes—State of the Art in Research)

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16 pages, 3986 KiB

Open AccessArticle

Optimization and Validation of a Method to Determine Enolones and Vanillin Derivatives in Wines—Occurrence in Spanish Red Wines and Mistelles

by Mónica Bueno, Julián Zapata, Laura Culleré, Ernesto Franco-Luesma, Arancha de-la-Fuente-Blanco and Vicente Ferreira

Molecules 2023, 28(10), 4228; https://doi.org/10.3390/molecules28104228 - 22 May 2023

Cited by 1 | Viewed by 1151

Abstract

Understanding the chemical nature of wine aroma demands accurate quantitative determinations of different odor-active compounds. Quantitative determinations of enolones (maltol, furaneol, homofuraneol, and sotolon) and vanillin derivatives (vanillin, methyl vanillate, ethyl vanillate, and acetovanillone) at low concentrations are complicated due to their high [...] Read more.

Understanding the chemical nature of wine aroma demands accurate quantitative determinations of different odor-active compounds. Quantitative determinations of enolones (maltol, furaneol, homofuraneol, and sotolon) and vanillin derivatives (vanillin, methyl vanillate, ethyl vanillate, and acetovanillone) at low concentrations are complicated due to their high polarity. For this reason, this paper presents an improved and automated version for the accurate measure of these common trace wine polar compounds (enolones and vanillin derivatives). As a result, a faster and more user-friendly method with a reduction of organic solvents and resins was developed and validated. The optimization of some stages of the solid phase extraction (SPE) process, such as washing with an aqueous solution containing 1% NaHCO₃ at pH 8, led to cleaner extracts and solved interference problems. Due to the polarity of these type of compounds, an optimization of the large volume injection was also carried out. Finally, a programmable temperature vaporization (PTV) quartz glass inlet liner without wool was used. The injector temperature was raised to 300 °C in addition to applying a pressure pulse of 180 kPa for 4 min. Matrix effects were solved by the use of adequate internal standards, such as ethyl maltol and 3′,4′-(methylenedioxy)acetophenone. Method figures of merit were highly satisfactory: good linearity (r² > 0.98), precision (relative standard deviation, RSD < 10%), high recovery (RSD > 89%), and low detection limits (<0.7 μg/L). Enolones and vanillin derivatives are associated with wine aging. For this reason, the methodology was successfully applied to the quantification of these compounds in 16 Spanish red wines and 12 mistelles. Odor activity values (OAV) indicate that furaneol should be considered an aroma impact odorant in red wines and mistelles (OAV > 1) while homofuraneol and sotolon could also produce changes in their aroma perceptions (0.1 < OAV < 1). Full article

(This article belongs to the Special Issue Analytical Methods for Characterization and Isolation of Natural Products)

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17 pages, 2035 KiB

Open AccessArticle

Proteomic Signature of Extracellular Vesicles Associated with Colorectal Cancer

by Natalia Soloveva, Svetlana Novikova, Tatiana Farafonova, Olga Tikhonova and Victor Zgoda

Molecules 2023, 28(10), 4227; https://doi.org/10.3390/molecules28104227 - 22 May 2023

Cited by 1 | Viewed by 1925

Abstract

The proteins of extracellular vesicles (EVs) provide proteomic signatures that reflect molecular features of EV-producing cells, including cancer cells. Detection of cancer cell EV proteins is of great interest due to the development of novel predictive diagnostic approaches. Using targeted mass spectrometry with [...] Read more.

The proteins of extracellular vesicles (EVs) provide proteomic signatures that reflect molecular features of EV-producing cells, including cancer cells. Detection of cancer cell EV proteins is of great interest due to the development of novel predictive diagnostic approaches. Using targeted mass spectrometry with stable-isotope-labeled peptide standards (SIS), we measured in this study the levels of 34 EV-associated proteins in vesicles and whole lysate derived from the colorectal cancer (CRC) cell lines Caco-2, HT29 and HCT116. We also evaluated the abundance of 13 EV-associated proteins (FN1, TLN1, ITGB3, HSPA8, TUBA4A, CD9, CD63, HSPG2, ITGB1, GNAI2, TSG101, PACSIN2, and CDC42) in EVs isolated from blood plasma samples from 11 CRC patients and 20 healthy volunteers. Downregulation of TLN1, ITGB3, and TUBA4A with simultaneous upregulation of HSPG2 protein were observed in cancer samples compared to healthy controls. The proteomic cargo of the EVs associated with CRC represents a promising source of potential prognostic markers. Full article

(This article belongs to the Special Issue Mass Spectrometry in Biomarkers Discovery)

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17 pages, 8429 KiB

Open AccessArticle

Mössbauer and Structure-Magnetic Properties Analysis of A_yB_1−yC_xFe_2−xO₄ (C=Ho,Gd,Al) Ferrite Nanoparticles Optimized by Doping

by Qing Lin, Fang Yang, Qian Zhang, Kaimin Su, Huiren Xu, Yun He and Jinpei Lin

Molecules 2023, 28(10), 4226; https://doi.org/10.3390/molecules28104226 - 22 May 2023

Cited by 2 | Viewed by 973

Abstract

A_yB_1−yC_xFe_2−xO₄ (C=Ho,Gd,Al) ferrite powders have been synthesized by the sol-gel combustion route. The X-ray diffraction of the CoHo_xFe_2−xO₄ (x = 0~0.08) results indicated [...] Read more.

A_yB_1−yC_xFe_2−xO₄ (C=Ho,Gd,Al) ferrite powders have been synthesized by the sol-gel combustion route. The X-ray diffraction of the CoHo_xFe_2−xO₄ (x = 0~0.08) results indicated the compositions of single-phase cubic ferrites. The saturation magnetisation of CoHo_xFe₂₋_xO₄ decreased by the Ho³⁺ ions, and the coercivity increased initially and then decreased with the increase of the calcination temperature. The Mössbauer spectra indicated that CoHo_xFe₂₋_xO₄ displays a ferrimagnetic behaviour with two normal split Zeeman sextets. The magnetic hyperfine field tends to decrease by Ho³⁺ substitution owing to the decrease of the A–B super-exchange by the paramagnetic rare earth Ho³⁺ ions. The value of the quadrupole shift was very small in the CoHo_xFe_2−xO₄ specimens, indicating that the symmetry of the electric field around the nucleus is good in the cobalt ferrites. The absorption area of the Mössbauer spectra changed with increasing Ho³⁺ substitution, indicating that the substitution influences the fraction of iron ions at tetrahedral A and octahedral B sites. The X-ray diffraction of Mg_0.5Zn_0.5C_xFe_2−xO₄(C=Gd,Al) results confirmed the compositions of single-phase cubic ferrites. The variation of the average crystalline size and lattice constant are related to the doping of gadolinium ions and aluminum ions. With increasing gadolinium ions and aluminum ions, the coercivity increased and the saturation magnetization underwent a significant change. The saturation magnetization of AlMg_0.5Zn_0.5FeO₄ ferrite reached a minimum value (M_S= 1.94 mu/g). The sample exhibited ferrimagnetic and paramagnetic character with the replacement with Gd³⁺ ions, that sample exhibited paramagnetic character with the replacement with Al³⁺ ions, and the isomer shift values indicated that iron is in the form of Fe³⁺ ions. Full article

(This article belongs to the Special Issue Magnetic Nanomaterials: Modern Trends and Prospects)

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